Issue 19, 2008
From the journal:

Dalton Transactions

Structure, formation and catalytic studies of a meso-palladioporphyrin intermediate in a Heck reaction†

Michael Y. Jiang,a   Ji-Young Shin,a   Brian O. Patricka  and  David Dolphin*a  

* Corresponding authors

a Department of Chemistry, University of British Columbia, Rm W300-6174 University Blvd., Vancouver, BC, Canada
E-mail: david.dolphin@ubc.ca
Fax: +1-604-822-9278
Tel: +1-604-822-4571

Abstract

A meso-palladioporphyrin intermediate was isolated from a Heck reaction between an iodoporphyrin and a non-activated olefin using a Pd(PPh3)2Cl2/Et3N system; its structure was characterized by NMR, MS and X-ray crystallography. Studies on its formation indicate that the Pd(II) catalyst was reduced in situ by Et3N with the assistance of water. The catalytic activity of the intermediate was confirmed by stoichiometric and catalytic reactions using a more reactive olefin, ethyl acrylate.

Graphical abstract: Structure, formation and catalytic studies of a meso-palladioporphyrin intermediate in a Heck reaction

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Article information

DOI
https://doi.org/10.1039/B801163J
Article type
Paper
Submitted
22 Jan 2008
Accepted
21 Feb 2008
First published
26 Mar 2008

Dalton Trans., 2008, 2598-2602

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Structure, formation and catalytic studies of a meso-palladioporphyrin intermediate in a Heck reaction

M. Y. Jiang, J. Shin, B. O. Patrick and D. Dolphin, Dalton Trans., 2008, 2598 DOI: 10.1039/B801163J

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